While in Los Angeles, Benson began doing stand-up after he and two other friends dared each other to. One of them didn't show, and the other one signed up too late. Benson claimed that "I went in anyway and did my three minutes of whatever I could come with and people actually laughed."[4] At the age of 22, Benson began performing regularly as a stand-up comedian; however, it wasn't until 28 that he became a stoner, after a week's worth of gigs smoking pot afterwards alongside Brian Posehn and Greg Proops.[5] He made his earliest television appearances as a stand-up in the late 1980s and early 1990s on programs such as Comedy Central's The A-List and Two Drink Minimum and was one of the featured comedians in the cast of Joel Hodgson's sketch-comedy pilot The TV Wheel which aired on Comedy Central in 1995. One of Benson's earliest jobs in television was writing for the MTV game-show Trashed in 1994.

On August 4, 2009, Benson's second album, Unbalanced Load, was released by Comedy Central Records. His third album, Hypocritical Oaf was released on August 31, 2010. Benson aims to record a new album every April 20 (with a subsequent summer release date) for as many consecutive years as possible.[6] Benson's fourth album, Potty Mouth, was released on August 29, 2011. The pattern continued with the release of his fifth album, Smug Life, which was released on July 3, 2012, and Gateway Doug, his sixth album, released on July 9, 2013. On July 8, 2014, Doug released a sequel to Gateway Doug entitled Gateway Doug 2: Forced Fun. His latest album release is Promotional Tool which came out on June 9, 2015.

A regular feature of the podcast is the Leonard Maltin Game, which has been described as Name That Tune with movies instead of songs.[7] The game consists of Benson reading excerpts from a Leonard Maltin review and guests wagering how many names, read from the bottom of the cast list up, it would take for them to identify the movie.

Other regular features of the podcast include the segments Tweet Relief: Tweets About Movies, Watch This/Not That, Not for Emetophobes, and From the Corrections Department, as well as the games Build a Title, Name a Movie, A-B-C-Deez Nuts, How Much Did This Shit Make?, Lincoln or Bane?, Love, Like, Hate, Hate-Like, Doing Lines with Mark Wahlberg, The Seth Rogen Game (A.K.A. Last Man Stanton), Whose Tagline Is It Anyway, Now Buscemi Now You Don't, Tell The Truth! and F Marry Kill: Movies.

At the conclusion of many of the early podcasts, Doug would state "As always, Willem Dafoe is a Shithead," which resulted in so many people wondering about why, that Google searches began to automatically complete the phrase as a suggested match. The Willem Dafoe comment started as a joke based on the fact that it would seemingly be the only bad words ever uttered about Dafoe, but many people didn't catch on and, after explaining it a few times, Benson decided to let Dafoe rest. Now, the runners up in the Leonard Maltin game are allowed to name one shithead as a consolation prize.

In 2010, Benson started an annual, 2 hour Twelve Guests of Christmas special every holiday season. This episode features 12 guests (occasionally more) rather than the usual 3 guests and they play an elimination style Leonard Maltin Game. Scott Aukerman won the first year, while Graham Elwood dominated the next two years in a row.[8] The 2013 champion was podcast fan and Pardcast-A-Thon auction winner, Sean Sakimae. Sakimae also qualified for the next Tournament of Champions for naming the film Titanic in negative names and winning the game.[9]Riki Lindhome beat Jimmy Pardo in the finals of the 2014 edition when Pardo couldn't get the name Lori Singer when going negative three on Footloose. Scott Aukerman bested Sarah Silverman for his second win in 2015.

In 2008, Benson was the protagonist of the film Super High Me (a play on the name and concept of the film Super Size Me), released on DVD on June 10, 2008. In the movie, Benson compares the results of not smoking any marijuana at all for 30 days versus the effects of smoking as much marijuana as possible for the same amount of time.[10] The film was produced by Red Envelope Entertainment. The results of the experiment were that it had little or no negative effects on Doug's health. Doug is currently suing the people who made the original film to stop a sequel. [11]

The show spun off into a monthly audio-only podcast on January 21, 2011, which took the TV show's format and altered it slightly by allowing the performances and conversations to play out in longer unedited episodes.

On December 29, 2009, Benson had a documentary special called The High Road with Doug Benson air on the G4 network. The special followed Benson and comedian Graham Elwood on one of their stand-up comedy tours.

On March 17, 2009, the host of the Fox News comedy program Red Eye w/ Greg Gutfeld along with Benson as a panelist, joked about Canadian Lieutenant General Andrew Leslie's statement that the Canadian Armed Forces may require a one-year "synchronized break" once Canada's mission in Afghanistan ends in 2011.[13] "Meaning, the Canadian military wants to take a breather to do some yoga, paint landscapes, run on the beach in gorgeous white Capri pants," Gutfeld said.[13] "I didn't even know they were in the war", added Benson, then continued, "I thought that's where you go if you don't want to fight. Go chill in Canada."[13] Gutfeld also said: "Isn't this the perfect time to invade this ridiculous country? They have no army!"[13]

The segment drew wide attention and outrage in Canada after being posted on YouTube following the reported deaths of four Canadian soldiers in Afghanistan three days earlier.[14][15][16] Canada, at the time, had been in command of the NATO mission in the Kandahar Province, the birthplace and former Taliban captital, for the past three years.[17] Along with the Helmand Province, the two provinces were "home to some of the fiercest opposition to coalition forces" and reported to "have the highest casualty rates per province."[18]

Canadian Defence Minister Peter MacKay called on Fox to apologize for the satirical comments, describing the remarks as "despicable, hurtful and ignorant."[19] Benson was scheduled to appear in Canada at Edmonton's The Comic Strip April 3–5, 2009, but the shows were canceled after the owner received threats of "bodily injury" toward the American comic. "Some were saying he wouldn't make it from the airport to the club. For everyone's safety, we decided it was best to avoid the scenario altogether," said manager Rick Bronson.[20] Benson offered an apology following the incident on CTV NewsPower Play with Tom Clark.[21] The comedian stated that he was "ignorant about the situation in Afghanistan" and that the timing of the jokes were "completely out of line".[21] "I honestly said things, in retrospect, I completely regret" said Benson and has vowed to "never appear on the show again".[21]